Reaction #1256773

Reaction equation

trans-4-[2-(4-isoxazolo[4,5-c]pyridin-3-yl-piperazin-1-yl)-ethyl]-cyclohexylamine dihydrochloride

AcOH

iPr2NEt

TBTU

→

title compound

Yield 67.0%

N-{trans-4-[2-(4-Isoxazolo[4,5-c]pyridin-3-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-acetamide

Yield 67.0%

Solvents

dioxane

Conditions

Workup

1. 1
   OtherAfter evaporation to dryness sat. aq. NaHCO3
2. 2
   workup.ADDITIONwas added
3. 3
   Extractionthe product was extracted with 2 portions of CH2Cl2

Procedure

A mixture in dioxane (5 ml) of trans-4-[2-(4-isoxazolo[4,5-c]pyridin-3-yl-piperazin-1-yl)-ethyl]-cyclohexylamine dihydrochloride (100 mg, 0.25 mmol), AcOH (22 mg, 0.37 mmol), iPr2NEt (161 mg, 1.2 mmol) and TBTU (96 mg, 0.30 mmol) was stirred 16 h at r.t. After evaporation to dryness sat. aq. NaHCO3 was added and the product was extracted with 2 portions of CH2Cl2. The organic layers were directly loaded on a column. Flash chromatography (20 g SiO2, CH2Cl2/MeOH 100:0→90:10) yielded 62 mg (67%) of the title compound as white solid. m/z=372.2 ([M+H]+).

Source